Tributylborane → HCID 67012329, 화합물

HRID 2056607노트

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HRID 2056607 반응식
[CH3:1][CH:2]([CH3:32])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27](C)(=[O:29])=[O:28])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1)=[O:7].C[Mg]Cl.C(B(CCCC)CCCC)CCC.C([O-])(=O)C.[Na+].[NH2:54]OS(O)(=O)=O>C1COCC1.C(OCC)(=O)C.O>[CH3:1][CH:2]([CH3:32])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27](=[O:29])(=[O:28])[NH2:54])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1)=[O:7]

참가 물질

9

반응물 5

HCID 31216TributylboraneHCID 76284hydroxylamine-O-sulfonic acidHCID 517045Sodium AcetateHCID 668499076-[4-(2-METHANESULFONYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (3-METHYLBUTYL)AMIDEHCID 178418332HCID 178418332, 화합물

생성물 1

HCID 67012329HCID 67012329, 화합물수율 42.1%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To an ice-cold solution of 6-[4-(2-methanesulfonylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (3-methylbutyl)amide (0.078 g, 0.17 mmol) in 5 mL of THF cooled was added methyl magnesium chloride (0.071 mL, 0.212 mmol). The resulting mixture was stirred for 15 minutes at 0° C., and then 30 minutes at ambient temperature. The reaction mixture was cooled to 0° C. again, then tributylborane (0.255 mL, 0.255 mmol) was added. The mixture was stirred at ambient temperature for 30 minutes, then heated to reflux for 18 h. After the mixture was cooled to 0° C., sodium acetate, water and hydroxylamine-o-sulfonic acid (0.067 g) were added. The mixture was stirred for 3 h, and then diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine, dried and concentrated in vacuo. The residue was purified by flash column chromatography using 20% methanol in ethyl acetate to yield the title product (0.033 g, 42% yield). 1H NMR (300 MHz, CDCl3) δ 8.58, 7.98, 7.81, 7.75-7.68, 7.64-7.58, 7.43, 7.19, 4.03-3.88, 3.78-3.59, 3.21-3.20, 3.152-3.147, 1.65-1.50, 1.46-1.35, 0.85. 13C NMR (75 MHz, CDCl3) δ 170.1, 165.5, 161.7, 146.3, 139.1, 137.3, 135.5, 131.3, 130.9, 128.8, 127.9, 114.4, 45.6, 45.2, 44.96, 42.6, 39.5, 38.8, 27.1, 22.9. MS (ES+) m/z 460.1 (M+1).

후처리

  1. custom30 minutes
  2. customat ambient temperature
  3. temperatureThe reaction mixture was cooled to 0° C. again
  4. stirringThe mixture was stirred at ambient temperature for 30 minutes
  5. temperatureheated
  6. temperatureto reflux for 18 h
  7. temperatureAfter the mixture was cooled to 0° C.
  8. stirringThe mixture was stirred for 3 h
  9. washwashed with saturated sodium bicarbonate, brine
  10. customdried
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-e49d8c9416d04fc4af66fa2da6bb0595
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07335658B2

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